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The small town of Kennebunkport, Maine, is home to some big money. Habitués include the straight-backed and the well-heeled who keep themselves — and their net worth — to themselves. Collars may be popped and yachts may be vintage but large five-bedroom houses on the oceanfront are quietly referred to as “cottages”. Wealth in Kennebunkport is low-key; one can procure a lobster roll from the McDonald’s drive thru for $7.99.

The town is a bucolic picture of outdoor living: sailing a schooner out to sea, toasting s’mores on balmy summer evenings, dashing through the snow in winter. Yet a particular quirk of Kennebunkport is that every day of the summer season sightseers line Ocean Avenue, peering through binoculars at a rocky promontory out in the Atlantic. They are looking at Walker’s Point, the summer home of George HW Bush, hoping for a glimpse of the 41st president and his progeny. World leaders have also converged on the tiny town over the years at the invitation of the Bush family, including Margaret Thatcher, Mikhail Gorbachev and Vladimir Putin, whose 2007 talks with the then president George W Bush, were dubbed the “lobster summit”.

The town has long been thought of as the kind of place its citizens could paddle board their way through retirement. Yet after its property market began to decline in the early 2000s, Kennebunkport has been trying to make the transition from summer colony to year-round destination.

“The area has certainly grown up,” says Heather Motes, owner of Sand Dollar Real Estate. “Seasons have extended and there are more events and activities attracting people throughout the year.” The town is 30 miles from Portland, and 90 miles from Boston, which makes commuting — at least for part of the week — a possibility.

Steve Kingston agrees the town has changed. He owns The Clam Shack, a small, white clapboard hut by the bridge over the Kennebunk river that is something of a local institution. “Twenty-five years ago a lot of businesses would board up at the end of a relatively short summer season,” he says, but not so any more.

Local agents think this has helped bolster the property market. Last year the median price for a house sold in the Kennebunks — the name given to Kennebunkport and its neighbour Kennebunk — reached $360,000; up 20 per cent since the market low in 2010. That said, Christopher Lynch, president of Legacy Properties, admits that the market is still catching up to where it was in 2004.

Kennebunkport was historically a fishing village until a shipbuilding boom on the Kennebunk river in the 1800s turned it into one of the wealthiest towns in New England. Today, coastal villages such as Cape Porpoise, east of Kennebunkport, are still working fishing harbours. In Maine the lobster market alone exceeds $300m a year; wake up at 6am and you can watch the lobstermen on the jetty getting ready to set off for the day.

Although Cape Porpoise is home to a working middle-class community, houses can sell for as much as $5m. Century 21 is marketing an arts-and-crafts-style home there with views towards the ocean for $4.1m.

On Poet’s Lane, near Cape Arundel, Legacy Properties has a four-bedroom house on sale for $1.97m, which comes with an outdoor pool and the kind of flag-adorned port-cochere that makes the driveway resemble that of the White House. In the Sea Grass neighbourhood, Kennebunk Beach Realty is selling a three-bedroom home on Ebb Tide Lane for $2.2m.

Notwithstanding the efforts to make Kennebunkport attractive all-year round, the quintessential old-money feel remains — you can spot the Ivy League upper crust by the whale logos of preppy brand Vineyard Vines on their shirt fronts. Yet Steve Kingston insists the town doesn’t have the usual divide between locals and “summer people”, which is often found in other New England coastal towns. “A lobsterman and a guy with a whale on his shirt will sit at a bar and have a beer together,” he says. “There’s a humbleness to the place.”